Methanol → HCID 22610213, compound

HRID 1860299Notes

Reaction equation

HRID 1860299 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:7]2[CH2:6][C:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([C:13](O)=[O:14])[CH2:4][C:3]1=2.CSC.B.CO>C1COCC1>[CH3:12][C:8]1([CH3:11])[CH2:9][CH2:10][C:2]([CH3:1])([CH3:21])[C:3]2[CH2:4][C:5]([CH2:13][OH:14])([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:6][C:7]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 22610217HCID 22610217, compound

Product 1

HCID 22610213HCID 22610213, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.5 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid were dissolved in 35 ml of THF and treated dropwise at room temperature with a solution of 1.4 ml of borane methylsulfide in 10 ml of THF. The reaction mixture was stirred for 2 hours, then treated dropwise with 13 ml of methanol and evaporated. The yellow, oily residue was purified with flash chromatography (silica gel, hexane/ethyl acetate=5:1) to yield 2.9 g of (4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-methanol as colorless oil.

Workup

  1. customevaporated
  2. customThe yellow, oily residue was purified with flash chromatography (silica gel, hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b5f36c7932e247c3ae58f3d7ec2d4021
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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